Sodium Carbonate → Ethyl 7-(3-pyridinyl)-3-azabicyclo[3.3.1]non-6-ene-3-carboxylate

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a solution of ethyl 7-(trifluoromethylsulfonyloxy)-3-azabicyclo[3.3.1]non-6-ene-3-carboxylate (0.34 g, 1.0 mmol) in dimethoxyethane (8 ml) was added saturated sodium carbonate solution (2.5 ml), lithium chloride (127 mg, 3.0 mmol) and pyridinylboronic acid (123 mg, 1.00 mmol). The flask was alternately evacuated and filled with argon three times. Then palladium tetrakistriphenylphosphine (23 mg, 0.02 mmol) was added and the evacuate/fill procedure performed once again. The flask was then sealed under argon and the stirred reaction mixture was heated at 95° C. for 2 h. The mixture was cooled to room temperature and then diluted with ether (10 ml) and filtered through a Celite pad. The Celite was washed with 30% ammonium hydroxide (25 ml) and ether (50 ml). The combined filtrates were separated into organic and aqueous phases, and the aqueous layer was extracted with ether (1×25 ml). Chloroform (20 ml) was added to the combined organic layers, and the mixture was dried over sodium sulfate and filtered. Concentrated of the filtrate by rotary evaporation, followed by purification of the residue (207 mg) by column chromatography, using a gradient of chloroform/methanol (0 to 2% methanol) as eluent, gave a light yellow oil (90 mg, 33%).

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